Luteolin-7-neohesperidoside - Compound Card

Luteolin-7-neohesperidoside

Select a section from the left sidebar

Luteolin-7-neohesperidoside

Structure
Zoomed Structure
  • Family: Plantae - Verbenaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(C)[C@@H]([C@@H](C1O)O)O
InChI InChI=1S/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9?,18?,20-,21+,22-,23-,24?,25?,26-,27+/m0/s1
InChIKey SHPPXMGVUDNKLV-IPFKXTELSA-N
Formula C27H30O15
HBA 15
HBD 9
MW 594.52
Rotatable Bonds 6
TPSA 249.2
LogP -1.39
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 594.16
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Verbena officinalis Verbenaceae Plantae 79772

Showing of synonyms

  • Kawashty SA, El-Garf IA (2000). The flavonoid chemosystematics of Egyptian Verbena species. Biochemical Systematics and Ecology,2000,28(9),919-921. [View] [PubMed]
Pubchem: 44258083
Nmrshiftdb2: 60065722

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.64
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.33
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
57.51
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.18
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.65
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-9072.91
Rat (Acute)
2.24
Rat (Chronic Oral)
4.15
Fathead Minnow
20.09
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
516.11
Hydration Free Energy
-3.02
Log(D) at pH=7.4
-0.09
Log(P)
-0.07
Log S
-4.92
Log(Vapor Pressure)
-12.22
Melting Point
216.36
pKa Acid
4.3
pKa Basic
6.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9395
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9395
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.9113
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.9113
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9046
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9046
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8971
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8971
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8924
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8924
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8901
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8901
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8872
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8872
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8792
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8792
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8772
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8772
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8591
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8591
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8539
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8539
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8418
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8418
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8395
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8395
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8354
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8354
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8289
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8289
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8085
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8085
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8050
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8050
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7996
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 4 0.7996
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7900
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7900
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7894
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7894
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7868
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7868
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7838
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7838
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7815
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7815
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7810
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7810
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7764
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7764
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7740
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7740
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7714
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7714
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7707
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7707
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7696
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7696
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7693
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7693
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7689
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7689
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7689
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7689
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7681
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7681
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7593
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7593
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7545
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7545
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7497
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7496
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7496
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7495
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7495
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7480
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7480
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7480
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7480
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7450
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7450
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7423
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7423
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7401
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7401
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7393
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7393
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7348
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7348
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7340
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7340
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7314
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7314
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7294
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7294
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7260
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7260
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7249
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7249
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7231
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7231
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7201
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7201
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7165
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7165
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7133
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7133
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7113
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7113
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7098
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7098
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7089
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7089
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7077
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7077
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7077
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7077
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7073
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7073
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7067
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7067
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7060
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7060
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7056
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7056
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7044
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7044
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7022
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7022
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7021
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7021
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7019
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7019
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7017
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7017
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7013
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7013
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7004
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7004
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7003
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7003
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7003
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7003
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7003
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7003
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7000
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7000

Download SDF